SU799651A3 - Способ получени амидов -кето-КАРбОНОВыХ КиСлОТ - Google Patents

Способ получени амидов -кето-КАРбОНОВыХ КиСлОТ Download PDF

Info

Publication number: SU799651A3
Authority: SU; USSR - Soviet Union
Prior art keywords: water; acid; mol; yield; amide
Prior art date: 1977-02-25

Application number

SU772489902A

Other languages

English (en)

Russian (ru)

Inventor

Клееманн Аксель

Кленк Херберт

Шварце Вернер

Original Assignee

Дегусса (Фирма)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-02-25

Filing date

1977-06-02

Publication date

1981-01-23

1977-06-02 Application filed by Дегусса (Фирма) filed Critical Дегусса (Фирма)

1981-01-23 Application granted granted Critical

1981-01-23 Publication of SU799651A3 publication Critical patent/SU799651A3/ru

Links

238000000034 method Methods 0.000 title claims abstract description 12
AHAXISXGFCFQGE-UHFFFAOYSA-N n-oxoformamide Chemical class O=CN=O AHAXISXGFCFQGE-UHFFFAOYSA-N 0.000 title 1
150000001408 amides Chemical class 0.000 claims abstract description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 13
229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 11
239000000203 mixture Substances 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
239000003960 organic solvent Substances 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
-1 keto acid nitrile Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 10
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
239000013078 crystal Substances 0.000 claims description 6
150000002825 nitriles Chemical class 0.000 claims description 5
238000003756 stirring Methods 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
239000012074 organic phase Substances 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims 1
230000008020 evaporation Effects 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000011541 reaction mixture Substances 0.000 claims 1
230000002269 spontaneous effect Effects 0.000 claims 1
239000002904 solvent Substances 0.000 abstract description 5
125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
125000004432 carbon atom Chemical group C* 0.000 abstract 7
125000004965 chloroalkyl group Chemical group 0.000 abstract 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
125000001188 haloalkyl group Chemical group 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
150000001264 acyl cyanides Chemical class 0.000 abstract 1
229910052799 carbon Inorganic materials 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
239000007788 liquid Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical class CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
230000003993 interaction Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZRUTYWGJKZWINV-UHFFFAOYSA-N 2-(2,2-dichloro-1-methylcyclopropyl)-2-oxoacetamide Chemical compound NC(=O)C(=O)C1(C)CC1(Cl)Cl ZRUTYWGJKZWINV-UHFFFAOYSA-N 0.000 description 1
NAAAGRKNTBUEKN-UHFFFAOYSA-N 2-(2,2-dichloro-1-methylcyclopropyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1(C)CC1(Cl)Cl NAAAGRKNTBUEKN-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
GKGFKMQIBYSGEI-UHFFFAOYSA-N 2-formyl-3-methylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1C=O GKGFKMQIBYSGEI-UHFFFAOYSA-N 0.000 description 1
GZTZLYWUGFZVSM-UHFFFAOYSA-N 2-methylpropanoyl cyanide Chemical compound CC(C)C(=O)C#N GZTZLYWUGFZVSM-UHFFFAOYSA-N 0.000 description 1
HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
DSCLUUFQAFXSTA-UHFFFAOYSA-N 5-chloro-2-oxopentanamide Chemical compound NC(=O)C(=O)CCCCl DSCLUUFQAFXSTA-UHFFFAOYSA-N 0.000 description 1
241000209761 Avena Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
OXFVCMMQMWINHL-UHFFFAOYSA-N cyclopropanecarbonyl cyanide Chemical compound N#CC(=O)C1CC1 OXFVCMMQMWINHL-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940093476 ethylene glycol Drugs 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU772489902A 1977-02-25 1977-06-02 Способ получени амидов -кето-КАРбОНОВыХ КиСлОТ SU799651A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2708184A DE2708184C3 (de)	1977-02-25	1977-02-25	Verfahren zur Herstellung von a -Ketocarbonsäureamide!! (A)

Publications (1)

Publication Number	Publication Date
SU799651A3 true SU799651A3 (ru)	1981-01-23

Family

ID=6002152

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU772489902A SU799651A3 (ru)	1977-02-25	1977-06-02	Способ получени амидов -кето-КАРбОНОВыХ КиСлОТ

Country Status (12)

Country	Link
US (1)	US4161491A (fr)
JP (1)	JPS6050185B2 (fr)
AT (1)	AT348502B (fr)
BE (1)	BE855256A (fr)
CH (1)	CH627437A5 (fr)
DD (1)	DD131369A5 (fr)
DE (1)	DE2708184C3 (fr)
FR (1)	FR2381744A1 (fr)
GB (1)	GB1539320A (fr)
IL (1)	IL52238A (fr)
NL (1)	NL7706160A (fr)
SU (1)	SU799651A3 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2733181B2 (de) *	1977-07-22	1979-08-30	Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt	Verfahren zur Herstellung von N-substituierten a -Ketocarbonsäureamiden
DE3003542A1 (de) *	1980-01-31	1981-08-06	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von trimethylbrenztraubensaeureamid
US5916922A (en) *	1996-12-03	1999-06-29	Eli Lilly And Company	Phenyl glyoxamides as SPLA2 inhibitors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2434507A (en) *		1948-01-13		Z-otloro-j-iminobutyronitrile

1977
- 1977-02-25 DE DE2708184A patent/DE2708184C3/de not_active Expired
- 1977-05-31 BE BE6046034A patent/BE855256A/fr not_active IP Right Cessation
- 1977-06-02 AT AT392677A patent/AT348502B/de not_active IP Right Cessation
- 1977-06-02 SU SU772489902A patent/SU799651A3/ru active
- 1977-06-02 US US05/802,903 patent/US4161491A/en not_active Expired - Lifetime
- 1977-06-03 IL IL52238A patent/IL52238A/xx unknown
- 1977-06-03 NL NL7706160A patent/NL7706160A/xx not_active Application Discontinuation
- 1977-06-03 CH CH690377A patent/CH627437A5/de not_active IP Right Cessation
- 1977-06-03 JP JP52065653A patent/JPS6050185B2/ja not_active Expired
- 1977-06-03 FR FR7717127A patent/FR2381744A1/fr active Granted
- 1977-06-03 DD DD7700199298A patent/DD131369A5/xx unknown
- 1977-06-03 GB GB23668/77A patent/GB1539320A/en not_active Expired

Also Published As

Publication number	Publication date
JPS6050185B2 (ja)	1985-11-07
AT348502B (de)	1979-02-26
IL52238A (en)	1980-11-30
CH627437A5 (de)	1982-01-15
ATA392677A (de)	1978-07-15
US4161491A (en)	1979-07-17
IL52238A0 (en)	1977-08-31
GB1539320A (en)	1979-01-31
FR2381744A1 (fr)	1978-09-22
DE2708184A1 (de)	1978-08-31
JPS53105422A (en)	1978-09-13
FR2381744B1 (fr)	1980-01-18
DD131369A5 (de)	1978-06-21
NL7706160A (nl)	1978-08-29
DE2708184C3 (de)	1980-02-07
DE2708184B2 (de)	1979-06-07
BE855256A (fr)	1977-11-30

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